Young Tommy and Mature Cindy

Another thing that added to her growing obsession with young guys was Cindy's personal trainer. His name was Sebastian and he was only 20 years old. However, predictably, he was gay. He came over to Cindy's house four times a week for her weight training. Sebastian was extremely good looking and a real gentleman. He pushed Cindy and always complimented Cindy's body - without being sleazy. Cindy would've probably fucked him, but of course, that was never going to happen.

Over a number of weeks Cindy started to wonder if she could turn her fantasies into reality. She started to desire a young man - in the flesh. Looking through the dating sites, Cindy found many young guys looking for larger, older women, but after what happened with Greg, she couldn't bring herself to meet another guy through a dating site. Her sexual frustration was growing. Unfortunately, her vibrator and porn addiction merely intensified her frustration, rather than relieved it. Cindy desperately wanted to fuck a young guy. Cindy needed to fuck a young guy. However, she wasn't sure how to go about it. Many of the porn videos she watched were of pool-boys, or a young guy coming to assist an old lady. 'Surely I could make that happen. I'm sure there's a young man who could help me clean up the garden,' Cindy thought to herself.

Cindy couldn't get the idea out of her head. She explored the ways in which she could place an advert for someone to clean up the garden. The local university had an online notice board where people could request students for such a task. However, she was hesitant to invite someone she didn't know into her home. Then suddenly it hit her. There was a young guy working as an intern at the think-tank Cindy had been volunteering at. He worked in a different part of the office to Cindy, but every now and then she would see him at the kitchen near Cindy's desk. Tommy was very handsome. He was fair skinned, with short brown hair, brooding eyes, a beautiful smile, and a thin but athletic frame. Cindy knew he was only in Auckland for a short time, and was soon returning home. They had chatted briefly a couple of times. Each time they talked Tommy become a bit flustered. He was introverted, but a nice boy nonetheless. Cindy caught him stealing a glance at her body more than once. She felt as though there was some kind of connection.

The next day Cindy was in the office and she spotted Tommy as he walked into the kitchen. Her heart fluttered as he smiled at her briefly. She knew she had to do something. She knew she couldn't continue to pummel her pussy each night with a vibrator and not attempt to fulfil her fantasy. Cindy got up and walked towards him. She began to get nervous, as if she was a school girl with a crush.

"Just a coffee thanks Tommy. Two sugars, no milk." Cindy said cheekily as she walked up behind him.

Tommy turned around and flashed his smile at Cindy. "Sure thing Ms Santos. I just have to finish loading the dishwasher, then I'll make you a cup."

"Don't be silly Tommy." Cindy said quietly. "You're not the tea lady. I'll get my own."

"I don't mind." Tommy protested. "I'll bring it to your desk in a minute."

"You're a sweetie Tommy." Cindy said as walked out of the kitchen back to her desk.

Before long Tommy was at Cindy's desk with a hot cup of coffee. Black with two sugars.

"There you go Ms Santos." Tommy said as he placed the mug on her desk.

"Aww thanks Tommy." She said with a playful smile.

"Anytime Ms Santos." Tommy replied with a smile.

Tommy did well not to stare at Cindy's bulging chest, but he could feel his face turning red.

"This is your last week isn't it?" Cindy asked.

"Yeah, I head home a week today. To be honest, I'm not looking forward to going home, but I can't afford to stay here any longer. I'm going back to work and save money for uni next year."

"Are they not paying you enough to work here?" Cindy asked with a smile.

"Haha." Tommy laughed. "No, they don't pay me a cent. But to be fair I've learnt so much and it does look good on my CV. It's valuable, just not economically valuable."

Cindy paused. Her heart was racing. She had been thinking about this moment all day, and this was the perfect time.

"You know Tommy." Cindy said quietly. "If you want to earn a few dollars I do need my garden cleaned up. The leaves are starting to fall and I was going to hire someone to tidy things up. You keen for some work?"

"Yes!" Tommy replied excitedly, before blushing.

Cindy felt her face turning red too.

"Perfect." Cindy replied. "I'd much prefer you to a stranger in my house. How does Sunday sound? Give me your number and I'll text you the address so you know where I live."

"Suits me. I'm going back home the next day." Tommy replied with a smile as he wrote his number on a piece of paper.

And that was that. Cindy had scored herself a date. Well, a date of some sorts. Young Tommy had no idea about the thoughts swirling around in CIndy's mind. That evening Cindy poured herself a glass of wine, sat down with her phone, then messaged Tommy. Before long they agreed on Sunday at 3pm. Cindy grabbed her laptop from the nearby table and typed Tommy's number into Facebook. His profile popped up - Tommy Connell.

As Cindy scrolled through Tommy's profile she began to get a good picture of his personality. Some of which she already knew. He came from a smallish town in the South Island, he was interested in cities and the environment, and he loved tennis. One thing stood out to Cindy; Tommy's posts and comments were always kind. He only had nice things to say to other people. A few months ago his mom posted a photo of his 18th birthday on his timeline. It was an image of him blowing out his candles, while his proud mother stood in the background, almost in tears. 'Thanks for the party, love you xx' Tommy replied to his mom. Tommy appeared to be a genuinely nice boy. Just after his birthday he posted a picture of himself with his younger sister as they sat on a park bench eating ice-cream: 'Me and Lisa eating ice-cream in the sun... no surprises there.' Tommy was a kind and gentle soul, not pushy, and definitely not arrogant. He was a giver, not a taker. He seemed to respect others and everyone had nice things to say about him too.

The most recent post on his timeline included four pictures of Tommy on his summer vacation. Two of the pictures were of himself on the beach with his shirt off. His young, firm body looked delectable. Tommy was slim, well toned, but no real muscle definition. There wasn't a hair on his chest. Tommy was fit, young, and only 18 years old; just the kind of boy Cindy been fantasizing about.

Cindy felt her pussy tingle as she clicked from one picture to the next. Then, before she knew it, her hand slipped down to her snatch. The wetness surprised Cindy. She quickly went upstairs and grabbed her vibrator, before returning to the couch and Tommy's Facebook profile. She removed her clothes, got herself comfortable on the sofa, placed the computer on her stomach, and began pleasuring herself. One picture was especially enticing - Tommy stradling a canoe topless. Cindy rubbed the buzzing vibrator over her wet clit as she kept her eyes on Tommy. Occasionally she'd look at the other photos, before returning to the picture of Tommy on the canoe.

"Buzzzzzzzz." Was the only sound she could hear, but gradually her own breathing got deeper, and she'd occasionally let out a small whimper.

Cindy closed her eyes. She imagined Tommy's slender frame between her thick, soft thighs as he fucked her eager cunt.

"Yes Tommy." She groaned to herself as she kept her eyes closed.

Within a few short minutes she could feel an orgasm brewing.

"Ohhh Tommy." She groaned as her legs shook uncontrollably.

Cindy opened her eyes, looked at the photo of Tommy straddling the canoe, then orgasmed loudly on the sofa.

"Yes, Tommy, yes." She screamed as her vibrator and hand became covered in her pussy juice.

Cindy drilled her wet, horny snatch with the vibrator - in and out, in and out. The computer fell to the ground, and onto a thick rug. She could hear and feel the wetness as she pummeled herself. Once the orgasm subsided, Cindy looked down and saw how wet she was. She spread her thick thighs to reveal a wet patch on the sofa, then rather awkwardly, waddled over to a box of tissues that were on the table. She almost used the whole box of tissues to clean herself up, as well as the sofa, and the drops on the rug and floor between the sofa and the table. It was all down her legs. It was everywhere.

"My goodness Tommy." She sighed to herself after she'd cleaned up and sat back down.

After that slightly undignified moment Cindy knew she knew she had to fuck Tommy. She had to act on her desires. It was Monday and Tommy was coming to do her gardening in six days time on Sunday at 3pm. Perhaps it was the wine, or was it the post-masterbation glow? Cindy wasn't sure, but that evening she was very happy with herself.

The next day she went to her beautician to get herself waxed. Normally Cindy leaves a patch of pubic hair just above her snatch, but she decided to have a full brazilian. Cindy used to get a full brazilian all the time, so it wasn't anything new for her. She wanted to look her best for Tommy. Two days before Tommy's arrival, on Friday, she went and got her eyebrows and nails done. Cindy decided on bright red for her nails. Then on Saturday she got her hair cut. Cindy's hairdresser always made her wavy black hair look great. It was shoulder length, layered, easy to manage, and it framed her face perfectly.

Before Cindy knew it Sunday arrived. Tommy was due at 3pm and by lunchtime Cindy began to get nervous. 'What the hell am I doing?' She asked herself. But she kept calm by reminding herself that nothing had to happen. She could take it as it comes, and if Tommy only clears the leaves, then that's fine. Cindy put new sheets on the bed - red silk sheets to match her nails. She didn't exactly have a plan of how she could seduce Tommy. Getting him into the Jacuzzi would be ideal, or perhaps sitting down together for a drink after he'd finished cleaning the yard. Cindy honestly didn't know what she was going to do. She had no experience seducing a man. She planned to wear tight workout gear and do some yoga in the gym room, which overlooked the backyard. Cindy knew she looked good in her workout gear. Every curve on her body would be on show for Tommy.

At 3pm she got changed. Cindy put on a thin pair of white yoga pants. They were tight and thin. Underneath she wore a black g-string. Cindy looked in the mirror.

"My God." She gasped quietly.

The tight, white yoga pants accentuated her plump ass. She loved the way they fitted - the seam sat deep in her ass crack, thus accentuating the size of her bulbous behind. They were tight around her thick, powerful thighs, and they ended just below her knees. She wore a tight, light-blue top. The material was thicker than her pants. The lacy bra she wore underneath was slightly visible. She stood in front of the mirror to make sure everything looked OK.

"My goodness Cindy." She whispered to herself.

There was nowhere for her large curves hide. At the age of 64 she looked extremely sexy. Her 47-34-49 body looked amazing. The light-blue top she had on hugged tightly around her big GG breasts. Meanwhile, her 49 inch waist stretched firmly against her white pants. Over the years gravity had caused Cindy's breasts to drop slightly, but not as much as most women experience. Her boobs have always been very perky, and despite hanging down to her belly-button, they remained relatively firm and plump. On the other hand, her ass hadn't dropped at all. It was large and firm. Her stomach was soft and supple. Although her abdominals from yesteryear were long gone, her midsection remained relatively flat.

Cindy put on some eyeliner, did her eyelashes, then added a bit of lip-gloss. No need for anything more. Then the doorbell rang. Cindy felt her heart racing, but she calmed herself down. 'He's only here to pick up the leaves' she reassured herself.

Cindy opened the front door and there stood Tommy. He looked absolutely gorgeous. He smiled at Cindy and she stopped breathing. She felt her heart pounding. Tommy had such a cute smile. He had a bag slung over his shoulder and wore a pair of tracksuit pants, running shoes, and a hooded top. A bit scruffy, but he was here to pick up the leaves, and Cindy was more interested in what was under his clothes.

"Hi Ms Santos." He said, breaking the silence.

"Hi Tommy. I'm so glad you're here." Cindy replied as she blushed. "The yard is a mess."

"I'm glad I can help." Tommy replied with a grin.

Tommy was nervous. Standing in front of Cindy's house was very different to chatting with her in the office. Cindy looked absolutely stunning. He had to concentrate to ensure his eyes didn't drop down and stare at her massive tits. Some of his friends would consider Cindy too old and too fat, but not Tommy. He was drawn to plump, older women. Cindy looked as though she'd just stepped out of one of his fantasies. He spent a lot of time watching mature porn and jerking off to women around Cindy's age. His ideal woman was one over 50 years of age with big tits and a big ass. He felt his face flush red.

"Come through." Cindy finally said. "Leave your shoes on, they're fine."

Cindy walked back inside in front of Tommy. She made sure he had a good view of her big, bulging ass as they walked through to the living room, then out towards the sliding doors that open out onto the backyard.

"So you're not a gardener Ms Santos?" Tommy asked as he followed her through the house.

"Not in the slightest Tommy." Cindy replied as she continued walking. "It's only me living here and that means nothing gets done outside. So thanks for coming today."

"It's no problem." He replied as he stared with shock at Cindy's big, sexy ass.

Over the past few weeks Tommy thought about Cindy many times as he stroked his cock in the shower. He'd become quite obsessed with Cindy, but had never seen her dressed like that. He never thought he'd see her in yoga pants. As they walked through the house Cindy was able to catch Tommy's reflection on a mirror in the hallway. She was happy to see him staring down at her ass as it bobbled rhythmically in front of him.

"This is a very nice house Ms Santos." Tommy said.

"Thank you Tommy." Cindy replied. "This is what you get when you divorce a man who has too much money."

"Ha." Tommy replied quietly, a little unsure whether he should laugh.

They reached the big sliding door that opens out onto the deck and the backyard. Cindy's shoes and socks were at the foot of the door.

"You can leave your bag on that seat." She said as she nodded towards a seat behind them. "Just give me a second to get my shoes on and I'll show you what needs to be done outside."

Cindy bent down, kept her legs straight, and put on her socks. She then started to loosen the laces on her shoes. As she did this her oversized, curvaceous ass pointed towards Tommy. She glanced up while she was tying her laces and saw Tommy's reflection in the window. Tommy had put his bag down and was standing directly behind Cindy. She could see his eyes locked on her ass. Tommy couldn't stop looking at the g-string through her yoga pants. He felt his cock move and became concerned that he would soon have an embarrassing boner. Cindy took her time. Tommy looked out through the doors to the backyard in an attempt to control himself. As Cindy slipped on each shoe she could feel her ass sway from side to side. She glanced up at Tommy again through the reflection in the window and was disappointed to see Tommy looking through the glass doors.

"There." Cindy said as she stood up.

She opened the sliding door, but not fully. Standing sideways in the doorway, she left just enough room for Tommy to squeeze through.

"Come on, I'll show you what needs doing." Cindy said as she stood there.

Tommy hesitantly stepped forward, and as he moved through the door he brushed past her big, soft GG breasts. The feeling of her tits brushing against him excited Tommy. Cindy placed her hand on the small of his back as he moved past.

"You see the big canvas sack there and the rake." Cindy said as she followed him. "I need those leaves in that sack."

"Sure thing Ms Santos." Tommy said as he turned around smiling.

His gaze dropped down to Cindy's breasts, then quickly back up to her face. He couldn't help it. It was a reflex. He knew she saw him. It was just for a split second, but it was obvious. Tommy blushed again.

"Now, do you want a drink of water?" Cindy asked, as if she hadn't noticed his eyes on her chest.

"I'm fine at the moment, thanks." He responded, doing well to maintain eye contact.

"OK then. I'm about to do some yoga in the gym over there." Cindy said she I pointed to the gym room.

"Sounds good." He replied. "I'll let you know if I need anything."

"Please do." Cindy said with a smile.

Cindy walked over to the gym room and opened the sliding glass door. She glanced at herself in the mirror on the wall and gasped.

"My god Cindy." She whispered.

Her nipples were pressing through the fabric. 'How long have they been like that?' She wondered to herself. 'Did I look like this when I greeted him at the door, or was it when he brushed past me to come outside? No wonder he couldn't keep eye contact.' Cindy's heart began racing again. She looked out to see Tommy already hard at work, raking the leaves into piles. Cindy moved a bit closer to the window so Tommy could see her doing yoga, however, whenever she looked up he was busy working instead of watching her. A number of thoughts rushed through her head: 'Maybe he doesn't find me attractive... maybe he prefers skinny women... I'm too old for him.'

Tommy kept his head down and worked on raking the leaves into piles. He was too scared to look over towards Cindy. He felt guilty for staring at Cindy's tits and was worried she would be offended. Moreover, he was worried that his cock would turn hard if he looked at her again. After about 15 minutes of doing yoga and not receiving a glance from Tommy, Cindy noticed the weather turning. First it was gusts of wind, then suddenly it started to rain. Within a minute or so the rain became very heavy. Cindy watched Tommy struggling to get the piles of leaves into the canvas sack. He was getting drenched and the wind was blowing the piles of leaves away.

"Come inside Tommy!" Cindy yelled into the howling wind as she opened the sliding door.

Tommy glanced up at Cindy as he attempted to get the leaves into the sack.

"Just forget it Tommy." She yelled. "It's too windy. Quickly! Come here!"

Tommy reluctantly closed the canvas sack and tightened the top, then ran over to Cindy.

"It's OK Tommy." Cindy said as he finally stepped through the door and into the gym. "You cleaned up most of it, but you can't do anymore in weather like that."

Tommy stepped inside without saying anything. His hooded top was completely wet, as were his pants and shoes.

"You're soaked through Tommy!" Cindy exclaimed as she wrapped a towel around his head.

"Yeah, its cold out there Ms Santos." He responded as he shivered.

Tommy looked like a drowned rat. Cindy dried his hair with the towel. As she did this Tommy tried not to stare at Cindy's breasts again, or her ass for that matter.

"You'll need to get these clothes off." Cindy said. "Here, I'll give you a hand with your top."

Cindy let the towel fall to the ground, then grabbed the bottom of his wet hoodie.

"Lift your arms up." She said as she peeled up his top, as well as the shirt he had on underneath.

Tommy leaned forward as Cindy pulled off his clothes. It was a struggle getting his arms out, but they finally came. Tommy just stood there with his arms folded, shivering topless in his wet pants. He felt a bit embarrassed, but glad to be out of the weather.